Copper-Catalyzed Silacarboxylation of Internal Alkynes by Employing Carbon Dioxide and Silylboranes

被引:138
作者
Fujihara, Tetsuaki [1 ]
Tani, Yosuke [1 ]
Semba, Kazuhiko [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Kyoto 6158510, Japan
关键词
alkynes; carboxylation; copper; homogeneous catalysis; silylborane; C-H BONDS; DIRECT CARBOXYLATION; TERMINAL ALKYNES; PALLADIUM; HYDROCARBOXYLATION; SILABORATION; COMPLEXES; CLEAVAGE; TRANSFORMATION; BENZOSILOLES;
D O I
10.1002/anie.201207148
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Silalactones: The copper-catalyzed reaction of internal alkynes with (dimethylphenylsilyl)pinacolborane (Me 2PhSi-B(pin)) as the silicon source and CO 2 at atmospheric pressure afforded silalactones selectively in good to high yields. The silalactones can be used as substrates for the Hiyama cross-coupling reaction as demonstrated for one substrate. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11487 / 11490
页数:4
相关论文
共 51 条
  • [11] Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge?
    Cokoja, Mirza
    Bruckmeier, Christian
    Rieger, Bernhard
    Herrmann, Wolfgang A.
    Kuehn, Fritz E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8510 - 8537
  • [12] Palladium-Catalyzed Direct Carboxylation of Aryl Bromides with Carbon Dioxide
    Correa, Arkaitz
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (44) : 15974 - +
  • [13] REACTION OF A SILYL-COPPER REAGENT WITH ACETYLENES - A NEW SYNTHESIS OF VINYLSILANES
    FLEMING, I
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (06) : 276 - 277
  • [14] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES
    FLEMING, I
    NEWTON, TW
    ROESSLER, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2527 - 2532
  • [15] Nickel-Catalyzed Carboxylation of Aryl and Vinyl Chlorides Employing Carbon Dioxide
    Fujihara, Tetsuaki
    Nogi, Keisuke
    Xu, Tinghua
    Terao, Jun
    Tsuji, Yasushi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9106 - 9109
  • [16] Copper-Catalyzed Hydrocarboxylation of Alkynes Using Carbon Dioxide and Hydrosilanes
    Fujihara, Tetsuaki
    Xu, Tinghua
    Semba, Kazuhiko
    Terao, Jun
    Tsuji, Yasushi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) : 523 - 527
  • [17] Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide
    Huang, Kun
    Sun, Chang-Liang
    Shi, Zhang-Jie
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) : 2435 - 2452
  • [18] Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation
    Iannazzo, Laura
    Molander, Gary A.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (26) : 4923 - 4926
  • [19] Studies on organosilicon chemistry.: Part 145.: New method for introduction of a silyl group into α,β-enones using a disilane catalyzed by a copper(I) salt
    Ito, H
    Ishizuka, T
    Tateiwa, J
    Sonoda, M
    Hosomi, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) : 11196 - 11197
  • [20] (NHC)CuI (NHC = N-heterocyclic carbene) complexes as efficient catalysts for the reduction of carbonyl compounds
    Kaur, H
    Zinn, FK
    Stevens, ED
    Nolan, SP
    [J]. ORGANOMETALLICS, 2004, 23 (05) : 1157 - 1160